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Angewandte Chemie International Edition in English
Volumn 26, Issue 10, 1987, Pages 1034-1035
Enantioselective Synthesis of Methylfuranosides of Unnatural 3,6‐Dideoxy‐3‐methylaldohexoses from Lactates by Homoaldol Reactions
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EID: 84985580886     PISSN: 05700833     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.198710341     Document Type: Article
Times cited : (15)
References (30)
  • 3
    • 0000163012 scopus 로고
    • Die Homoaldol-Reaktion oder wie man Probleme der Regio- und Stereoselektivität in den Griff bekommt
    • Reviews
    • (1984) Angewandte Chemie , vol.96 , pp. 930
    • Hoppe, D.1
  • 9
    • 0001556230 scopus 로고
    • 5: [α] D20 = −63.1 (neat);, prepared by diisobutylaluminum hydride reduction [6a] of ethyl (S)‐2‐benzyloxypropionate [6b]
    • (1982) J. Org. Chem. , vol.47 , pp. 2179
    • Baker, D.C.1    Hawkins, L.D.2
  • 12
    • 84985539647 scopus 로고    scopus 로고
    • 3, δ):6 : 2.05 and 7: 2.65 (each s, OH) [8].
  • 14
    • 0000311605 scopus 로고
    • α-Deprotonierung eines α-chiralen 2-Alkenylcarbamats unter Retention und Lithium-Titan-Austausch unter Inversion - zur Homoaldol-Reaktion unter 1,3-Chiralitätsübertragung
    • 1 and 2 are chiral and configurationally stable at the reaction temperature; cf.
    • (1986) Angewandte Chemie , vol.98 , pp. 171
    • Hoppe, D.1    Krämer, T.2
  • 18
    • 84985549826 scopus 로고    scopus 로고
    • W = 0.052 for 2618 extinction‐corrected reflections with F>4σ(F). The absolute configuration (and thus the space group) was chosen to agree with the known configuration of 5. Further details of the crystal structure investigation are available on request from the Fachinformationszentrum Energie, Physik, Mathematik GmbH, D‐7514 Eggenstein‐Leopoldshafen 2 (FRG), on quoting the deposition number CSD‐52 585, the names of the authors, and the journal citation.
  • 19
    • 84985575430 scopus 로고    scopus 로고
    • The anomeric ratio here is determined kinetically. The acidic reaction mixtures isomerize at room temperature to give 1‐epi‐10 and 1‐epi‐11, respectively.
  • 22
    • 84985521400 scopus 로고    scopus 로고
    • Obtained from ent‐5, which was prepared from biotechnologically accessible (R)‐isobutyl lactate.
  • 24
    • 84954310868 scopus 로고    scopus 로고
    • 2Cl, pyridine, 24 h at 0°C→20°C; step (b)10 equiv. KOAc, 22 h at 120°C in DMSO, yield 40‐45% ent‐12 and ent‐13, respectively; partial thermal elimination of the acetates to give the furan, —Acetolyses or formolyses according to the method of Mitsunobu failed
    • Synthesis , vol.1981 , pp. 1
    • Mitsunobu, D.M.1

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